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Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

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posted on 2021-08-10, 14:09 authored by Bingbing Wang, Pan Peng, Wan Ma, Zhao Liu, Cheng Huang, Yangmin Cao, Ping Hu, Xiaotian Qi, Qingquan Lu
Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

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